


What it Took

by RedTabby



Category: Supernatural
Genre: Consent, Dean Winchester - Freeform, Destiel - Freeform, Eventual Smut, Fluff, Jealousy, Multi, Oral Sex, Relationship(s), Sam Winchester - Freeform, Sex, Smut, castiel - Freeform
Language: English
Status: Completed
Published: 2017-01-09
Updated: 2017-01-09
Packaged: 2018-09-15 21:23:04
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,673
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9257897
Author URL: https://archiveofourown.org/users/RedTabby/pseuds/RedTabby
Summary: You've had a long time crush on Sam Winchester.  Right when you decide you're ready to get over him, the unexpected happens.





	

“Cheers to another win,” Dean raises his pint of beer as you, Cas, and Sam join him, “Hey now, don’t forget to look the person in the eyes when you cheers them. Otherwise it’s 7 years of bad sex.” 

You snort into your beer at Dean’s joke and notice that he shoots a wink at Castiel, who blushes and takes a sip from his own mug.

You glance over to Sam to see if he saw it too. He looks at you, smiles, and continues to drink. The two of you had sensed something was going on between Dean and Cas, but neither of you had the courage to ask them. You discreetly draw an imaginary line in the air symbolizing a tally mark for only Sam to see. Just because you didn't directly ask Dean or Cas, didn’t mean you weren’t taking stock of flirty exchanges between them. 

The four of you were at a bar celebrating another successful salt and burn case.

“Anyone want to lose to me in pool?” Dean taunts.

“I don’t entirely understand the entertainment of knocking balls into pockets, but I will play,” Castiel gets up from your table and walks over to the pool tables with Dean, leaving you and Sam alone. You hear Dean reminding Cas to not use his grace to cheat.

“Common Sam, we need to ask them,” you plead.

“Not a chance,” Sam replies, “Dean tries too hard to cover it up with those girls he brings home… I wish he would come out to us. An angel is by far the best partner I could hope for my brother to have.”

“Alright, he better tell us soon though. Do you want any food?” you ask, changing the subject, “I’m starving. How do you feel about nachos?”

“Yea sounds good,” Sam brushes his fingers through his hair, taking the menu is his hand to give it a look. “Lets get wings too.” 

A pretty waitress comes up to the pair of you and shamelessly flirts with Sam while he orders. You and Sam weren’t together, but it didn't mean you didn't have feelings for him. Sam half-flirted back with her, and your heart felt tight in your chest.

You had joined the Winchester duo about a year and a half ago. Before then you were hunting alone. The brothers and Cas had collaborated with you on a large case. You made such a great team that they had invited you to move in with them. It didn’t take you long to fall for the handsome younger brother. Even though your nerves were sparking through you, you mustered up the courage to ask him if he would be interested in taking your friendship a step further. Being who he is, Sam let you down gently, explaining that he had a past that made it difficult for him to seek romance in his life. That was when you learned about Jessica and Ruby and you understood. You were okay with it. Things didn't become weird and you continued to be a prosperous team.  
Unfortunately for you, you couldn’t shake the feelings you had for Sam. Dean caught on of course, and you confided in him. He was open with you talking to him about it whenever you needed to.

You put the ill thoughts about the waitress from your mind and with them the jealously. You needed to get over him. “May we also have another round please?” You ask the her. Your beer was already over half gone.

She left to head back to the bar and sent your order to the kitchen.

“She seems nice,” you peer over your glass to Sam.

“What makes you say that?” he chuckles

“Nothing, just an observation,” you smile at him.

Sam pulls his laptop out of his bag and sets it on the table.

“Nope. No way Winchester. Put it away” you put your hand on top of the computer preventing him from opening it and looking for a new case. “Tonight is for relaxing. Why don’t you go over there and find out where our drinks are.”

He sighs and gets up to go over and stand at the bar across from the flirty waitress. You pick up his laptop and return it to his bag. Leaning back in your seat you take a look around the bar. Cas and Dean seemed to be having a good time and you could tell the waitress was glad that Sam came over for a chat. You look to your left and you see a familiar face making their way over to you.

“Y/n? Is that you?”

“Jeremy Miller. Well this is a surprise. What are you doing here?” you had not seen Jeremy in 6 years, since high school. Back them he was known for being the captain of the football and for being a ladies man. You had been to a few parties at his house before, but you would consider yourselves more acquaintances than friends. Still, it was nice to see a familiar face every once in a while.

“This is a surprise! Mind if I join you?”

“Not at all,” you gesture to the seat across from you, “So, what brings you here?” you were nearly halfway across the country from where you both grew up.

“I’m actually just visiting for the weekend. It’s a buddy’s bachelor party. Do you remember Davis?” he points somewhere over your shoulder. You turn to look and see about 7 loud guys at a table. You recognize the extra drunk one as Davis from your high school as well.

You laugh when you spot him, “Yea, I remember.”

“He met a girl from around here a couple of years ago. They tried the long distance thing, but eventually he moved here and proposed. The wedding is tomorrow.”

“Wow, I’ll have to go congratulate him,” you say turning around to look at the rowdy crew. When you turn back to Jeremy you notice his eyes had left your face and were trailing down your body. You shifted in your seat and crossed one leg over the other. He was as good looking now as he was in high school except with more maturity. You cleared your throat to make him regain his focus.

“Tell me y/n, you know why I’m here… why are you?” He leans toward you from across the table and props his chin on his hand.

“Work”, you reply.

“Oh yea? What do you do?” he asks.

“Um, I’m part of a… sales team”, it was the first thing that popped into your head. “for a company.”

“That’s interesting. What kind of –“ Sam had returned to the table with 2 beers. 

Just in time. You thought to yourself. “Sam this is Jeremy. We used to go to high school together.”

“Nice to meet you Jeremy”, Sam extends his hand to shake Jeremy’s. He sits next to you, swapping your empty glass for a full one. You thank him.

“Likewise”, says Jer, he was looking between Sam and you trying to figure out the relationship. “Sam, I gotta tell ya, you’re a lucky man. Y/n is a great girl. All the guys used to chase after her. Me included!”

“Not true. Not even a little.” You state and look at Sam, who raises an eyebrow at you. “And we’re not together... we’re colleagues. It’s us, Sam’s brother and another.” You say pointing to Dean and Cas who were deep into their game of pool.

“Ah I see, I see”, Jer seemed satisfied with the answer. He stands up, “Well, come over and say hi to the guys if you’d like. I’ll be over there. Nice meetin’ ya Sam.” He gives your arm a squeeze and makes his way back to the bachelor party.

“He seems nice”, Sam teases the same way I had teased about the waitress.

You make sassy face and playfully stick your tongue out at him.

When the food arrives we call Dean and Cas over. The four of us dig in and finish every last crumb and with it several more rounds of drinks. The bar you were at was pretty big. You eyes widen when you see that the next room over had karaoke. 

“Dean look, look!” you say, throwing your arm around him. It was no secret that Dean was a sucker for karaoke. You notice that the bachelor party had found themselves over there as well. You pay for your food and join the crowd in the karaoke room. Without hesitation Dean jumps on stage and chooses to serenade the crowd with a very animated version of “Eye of the Tiger”. Sam, Cas and you laugh and cheer him on. After a few more performances Dean was back on stage and this time was with the very inebriated Davis. They were hilarious together and the crowd was going wild. 

You’re dancing and enjoying yourself when you feel a hand slide along your back and secure itself at your waist. You jump and turn to see Jeremy standing close to you.

“Jer, you startled me!” you had to yell because the music was loud.

He laughs and apologizes. “Want to take a break for a bit?”

You nod and follow him to the bar. He orders shots for the both of you.

“Two jolly rancher shots please”, he says to the bartender.

“Make one of those a whiskey”, you say raising your eyebrow at him.

“Two whiskeys then,” he turns to you. “I could swear you liked the sweet stuff.”

You laugh, “Jer, my taste has changed a lot since high school. I’m surprised you remembered.” The group of girls you were close with back then always brought sweet tasting coolers to parties.

“I wasn’t lying when I said I used to chase ya”, he winks.

You give him a look “You did not.”

“Doesn’t matter, you were out of my league anyways”, he sips his whiskey, “Still are”. He bites his lip and looks at yours.

“Says the captain of the football team.” You joke with him. “Regardless, look at us now. Years later, at the same bar, in the middle of nowhere.”

“Cheers to that!” you both downed the remaining whiskey and shimmied your way to the dance floor. It was in the next room over from Karaoke. You waved at Sam and Cas as you passed, and pointed, indicating you were going to the dance floor. You felt your buzz grow and you knew the whiskey and several beers were catching up to you. Jeremy spun you around the dance floor and pulled you in close not taking his hands off your body. You closed your eyes and leaned back into him, swaying your hips with the music. He wasn’t Sam, but it didn’t mean you weren’t enjoying yourself. You continued dancing like this for a while. Your eyes were closed which heightened the sensation of Jer’s hands moving on your body. He leaned down and whispered something seductive in your ear before kissing your neck from behind. This caused your eyes to jolt open. When they did, the first thing you saw was Sam staring at you from across the bar. His face looked tense. Jer spun you around to face him. He kept one hand on the small of your back and brushed your hair out of your face with the other.

“You’re so beautiful y/n”, he says before holding your chin and planting a deep kiss on your lips. It had been a while since you had been kissed and this was really nice. He pulled back and studied your face to see if you wanted more. You must have looked dumb-founded because he laughed and cupped your face with both of his large hands and kissed you again. You had just closed your eyes to enjoy the kiss when you suddenly felt a huge force cause the hands to leave your face as you’re knocked to the floor.

You open them to see Cas rush over to help you up.

“Sammy, no!” Dean shouts and you notice that Jeremy and Sam are in a tangle of fists right behind you. The commotion caught the attention of the entire bachelor party who rush over to the scene.

In a panic you try to split the two up, pleading them to stop. While attempting to pull and push them away from one another you get forced back by Cas who effortlessly pulls Jeremy up off the ground and tosses him into his buddies. Dean grabs Sam and shoves him towards the door. Cas follows.

You stand on the dance floor alone, looking between both parties. Dean has dragged Sam outside and Cas was waiting for you at the door. You dash over to Jeremy and examine his face. You’re glad to see that the only thing hurt is his ego. You apologize to him, say goodbye by kissing him on the cheek, and briskly walk towards the door, which Cas holds open for you.

“What the hell was that Sam?” you shout as soon as you see him. Unlike Jeremy, he had a bruise forming on his cheekbone. 

He doesn’t respond and Dean rolls his eyes and gets in the impala. 

“Dean, you’ve been drinking”. Cas stands outside the driver’s door and hold out his hand to accept the key. Dean sighs and hands it to him, getting out of the car. Even though it was a cool night, your anger towards Sam was keeping you warm.

“There is a motel over there”, Sam nods in the direction of the building across the road, avoiding eye contact with you.

Dean pays for the rooms. Before you can protest he disappears with Cas into one and tells Sam to go talk to you. Sam opens the door to the room you have to share and beckons you to enter.

You walk in and cross your arms and wait for him to close the door. You were prepared to rip him a new one, considering you had never once intervened when he was with a girl. He had never kissed any of them…but still. He turned around to face you but kept his eyes lowered.

“I’m sorry y/n,” his voice sounds shaky. You could tell he was embarrassed by the whole thing.

You drop your arms and walk over to him. It was impossible for you to stay mad at him. You lift his chin slightly and peer up into his eyes. “Not cool, Sam. I was fine. I was having a good time. I didn’t need saving.”

“I know…that’s what bothered me” he tells you in a hushed voice.

“Sam, why?” 

He finally meets your gaze. His cheek was bruised pretty bad. He gently cups your face in his hands and leans in close. “Because y/n, seeing you in his arms…it wasn’t right… it should have been me. It should be me”. That was the first time Sam Winchester kissed you. 

“How long?” you ask.

He gets a puzzled look on his face. Clearly that wasn’t what he wanted to hear after his kiss. “How long what?”

“You knew how I felt about you. What I felt, and you didn’t. How long has it been since that changed?”

Sam drops his head guiltily, “Y/n, I’ve always had feelings for you. But what I said before came from somewhere real. Whenever I’m involved with someone they end up getting hurt, or I do. I didn't want to lose you or see us fall apart”. You could tell he was being honest. “But now,” he continues, “I need you. And I promise, I’m not going to let anything happen to you, or us... If you’ll let me”. 

As he spoke you were unable to help yourself. Your stomach began to knot and you were unsure if you felt upset, nervous, or excited. Upset, because it had taken seeing you pressed up against another man to get him to open up. Nervous, because the butterflies in your stomach were going crazy. Excited, because you had only ever pictured this moment in your dreams and it was finally coming true. He holds both of your hands in his and awaits your reply.

You answer him by wrapping your arms around his neck and passionately kissing him. You have wanted this for too long. His picks you up and you wrap your legs around his waist. One of his hands graps your bum for support and the other slides up your back to tangle itself in your hair. You part your lips slightly and allow his tongue to dance with yours. With you still around him he sits on the bed. Your hands are all over him, unsure where to begin. A part of you couldn’t believe it was happening. You kissed Sam with such appetite that it drew a moan from deep in his throat. You felt his member begin to stiffen below you. You pull back slightly and rest your forehead on his. His heart was pounding, as was yours. 

He looks at you, “Do you want this?” he asks through heavy breathing. His chest was rising and falling and you could see sweat staring to gleam on his perfect chest.

“I need this”. You lift your arms and he swiftly removes your shirt. 

His follows. It was barely over his head before he pulls his arms through to wrap them around your body pulling you closer. His lips busy on yours again. He traces his lips across your jaw, down your neck and collar bone. “Y/n you’re so perfect”.

Utter bliss is the only way to describe what your feeling. Sam continues to trail kisses around your neck and shoulders while you’re seated in his lap. You entwine your fingers through his hair and begin gyrating your hips into his lap. He groans in pleasure into your chest. You slip off him and push him backwards so he’s laying on the bed. You start to undo his belt and he gets the idea. His speedy hands do the work for you and he kicks his jeans off. In the mean time you had wriggled out of your own. You’re standing at the end of the bed in nothing but your silky panty. His eyes move over your body, drinking it in. He gives a primal groan - turning you on more - as he sits up and begins moving towards you. You stop him by placing a hand in his chest and guiding him back down to the bed. You crawl on top of him and slide his boxer-briefs off with you teeth. You can hear him cursing above you. You grasp his member and begin stroking it slowly at first. You can see precum already forming at the tip. You make eye contact with him as you lick playfully. His mouth hangs open slightly and his eyes are plagued with pleasure. You begin to lightly suck and swirl your tongue around him. You moving your head up and down with your hand following rhythm. You suck a bit harder each time your lips reach the head, making eye contact.

“Oh my god y/n, you’re amazing” Sam’s eyes are closed and his head drops back.

You continue pleasuring him for a bit longer before he lifts your face and meets your lips with his. He gently pulls you up towards him and lays you down. He moves between your legs and loops his fingers through your silk, pulling it off seductively. He spreads your knees apart and works his mouth on your most sensitive spot. Your body twinges and you whimper with desire. Sam devours you, expertly interchanging pressure with his mouth, tongue and fingers.

“Sam…Sam, I’m close…please, I need you”, you beg.

He hops off the bed and grabs a condom from his bag which he rolls over his erect member. He climbs back on top of you and lines himself with your entrance. He takes his time filling you, ensuring you adjust before continuing deeper. Once settled in he starts thrusting slowly, building momentum. It doesn't take you long for your muscles to pulse and tighten around him for your first orgasm. It ripples through you as you scream out his name. He doesn’t stop to allow you to come down. Instead he places your legs over his shoulders and secures both your hands above your head with one of his. You gasp as this position allows him even deeper entrance, resulting in profanities leaving your mouth. Fuck, he was incredible. After your second orgasm you wrestled to gain control on top. It was your turn to show him who was boss. His face morphed into ones you had never seen before but hoped you would see again soon. With them the words that motivated you to keep your pace steady. You rode him until you could tell he was near climax. Very near.

“I have an idea”, you told him as you elevated yourself off him, promptly removed the condom, and replaced yourself with your lips. 

He was thrusting into your mouth in time with your movements until his body arched and he came. It was warm and slightly salty but you didn’t care. You swallowed as he looked at you with an expression of awe. He opened his arms and drew you in close. His heart was pounding and his breathing was rapid and deep. Sam stroked your hair and lifted your face to his to give you another one of his perfect kisses. You smiled at one another and tittered in appreciation at the former events.

“Shower?” you ask.

“Definitely”, Sam responds and gets out of the bed, only to pick you up in his arms and carry you away to the shower. He sets you down.

“Sam?”

“Mhmm”, a soft smile on his face.

“I’m so yours” 

“As I am yours”, his kisses you again and turns the shower on.


End file.
